메뉴 건너뛰기




Volumn 9, Issue 3, 2014, Pages 643-648

Pre-mRNA splicing-modulatory pharmacophores: The total synthesis of herboxidiene, a pladienolide-herboxidiene hybrid analog and related derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; PLADIENOLIDE HERBOXIDIENE DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG; EPOXIDE; FATTY ALCOHOL; HERBOXIDIENE; MACROLIDE; MDM2 PROTEIN, HUMAN; PLADIENOLIDE B; PROTEIN MDM2; PYRAN DERIVATIVE; RNA PRECURSOR;

EID: 84896918727     PISSN: 15548929     EISSN: 15548937     Source Type: Journal    
DOI: 10.1021/cb400695j     Document Type: Article
Times cited : (57)

References (49)
  • 3
    • 80054793884 scopus 로고    scopus 로고
    • RNA splicing: Disease and therapy
    • Douglas, A. G. and Wood, M. J. (2011) RNA splicing: Disease and therapy Brief Funct. Genomics 10, 151-164
    • (2011) Brief Funct. Genomics , vol.10 , pp. 151-164
    • Douglas, A.G.1    Wood, M.J.2
  • 4
    • 84871924824 scopus 로고    scopus 로고
    • The development and application of small molecule modulators of SF3b as therapeutic agents for cancer
    • Webb, T. R., Joyner, A. S., and Potter, P. M. (2013) The development and application of small molecule modulators of SF3b as therapeutic agents for cancer Drug Discovery Today 18, 43-49
    • (2013) Drug Discovery Today , vol.18 , pp. 43-49
    • Webb, T.R.1    Joyner, A.S.2    Potter, P.M.3
  • 5
    • 0013394889 scopus 로고    scopus 로고
    • Mechanisms of alternative pre-messenger RNA splicing
    • Black, D. L. (2003) Mechanisms of alternative pre-messenger RNA splicing Annu. Rev. Biochem. 72, 291-336
    • (2003) Annu. Rev. Biochem. , vol.72 , pp. 291-336
    • Black, D.L.1
  • 6
    • 79952220808 scopus 로고    scopus 로고
    • Reduced fidelity of branch point recognition and alternative splicing induced by the anti-tumor drug spliceostatin A
    • Corrionero, A., Minana, B., and Valcarcel, J. (2011) Reduced fidelity of branch point recognition and alternative splicing induced by the anti-tumor drug spliceostatin A Genes Dev. 25, 445-459
    • (2011) Genes Dev. , vol.25 , pp. 445-459
    • Corrionero, A.1    Minana, B.2    Valcarcel, J.3
  • 7
    • 33751391836 scopus 로고
    • Herboxidiene: A potent phytotoxic polyketide from Streptomyces sp. A7847
    • Isaac, B. G., Ayer, S. W., Elliott, R. C., and Stonard, R. J. (1992) Herboxidiene: A potent phytotoxic polyketide from Streptomyces sp. A7847 J. Org. Chem. 57, 7220-7226
    • (1992) J. Org. Chem. , vol.57 , pp. 7220-7226
    • Isaac, B.G.1    Ayer, S.W.2    Elliott, R.C.3    Stonard, R.J.4
  • 8
    • 0031584924 scopus 로고    scopus 로고
    • Herboxidiene: Determination of absolute configuration by degradation and synthetic studies
    • Edmunds, A., Trueb, W., Oppolzer, W., and Cowley, P. (1997) Herboxidiene: Determination of absolute configuration by degradation and synthetic studies Tetrahedron 53, 2785-2802
    • (1997) Tetrahedron , vol.53 , pp. 2785-2802
    • Edmunds, A.1    Trueb, W.2    Oppolzer, W.3    Cowley, P.4
  • 10
    • 1842832148 scopus 로고    scopus 로고
    • Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. Taxonomy, fermentation, isolation and screening
    • Sakai, T., Sameshima, T., Matsufuji, M., Kawamura, N., Dobashi, K., and Mizui, Y. (2004) Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. I. Taxonomy, fermentation, isolation and screening J. Antibiot. 57, 173-179
    • (2004) J. Antibiot. , vol.57 , pp. 173-179
    • Sakai, T.1    Sameshima, T.2    Matsufuji, M.3    Kawamura, N.4    Dobashi, K.5    Mizui, Y.6
  • 11
    • 1842865013 scopus 로고    scopus 로고
    • Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. in vitro and in vivo antitumor activities
    • Mizui, Y., Sakai, T., Iwata, M., UENAKA, T., Okamoto, K., Shimizu, H., Yamori, T., Yoshimatsu, K., and Asada, M. (2004) Pladienolides, new substances from culture of Streptomyces platensis Mer-11107. III. In vitro and in vivo antitumor activities J. Antibiot. 57, 188-196
    • (2004) J. Antibiot. , vol.57 , pp. 188-196
    • Mizui, Y.1    Sakai, T.2    Iwata, M.3    Uenaka, T.4    Okamoto, K.5    Shimizu, H.6    Yamori, T.7    Yoshimatsu, K.8    Asada, M.9
  • 13
    • 84880530428 scopus 로고    scopus 로고
    • Enantioselective synthesis of pladienolide B and truncated analogues as new anticancer agents
    • Kumar, V. P. and Chandrasekhar, S. (2013) Enantioselective synthesis of pladienolide B and truncated analogues as new anticancer agents Org. Lett. 15, 3610-3613
    • (2013) Org. Lett. , vol.15 , pp. 3610-3613
    • Kumar, V.P.1    Chandrasekhar, S.2
  • 14
    • 0030466895 scopus 로고    scopus 로고
    • New antitumor substances, FR901463, FR901464, and FR901465. II. Activities against experimental tumors in mice and mechanism of action
    • Nakajima, H., Hori, Y., Terano, H., Okuhara, M., Manda, T., Matsumoto, S., and Shimomura, K. (1996) New antitumor substances, FR901463, FR901464, and FR901465. II. Activities against experimental tumors in mice and mechanism of action J. Antibiot. 49, 1204-1211
    • (1996) J. Antibiot. , vol.49 , pp. 1204-1211
    • Nakajima, H.1    Hori, Y.2    Terano, H.3    Okuhara, M.4    Manda, T.5    Matsumoto, S.6    Shimomura, K.7
  • 16
    • 0030461311 scopus 로고    scopus 로고
    • New antitumor substances, FR901463, FR901464, and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties, and biological activities
    • Nakajima, H., Sato, B., Fujita, T., Takase, S., Terano, H., and Okuhara, M. (1996) New antitumor substances, FR901463, FR901464, and FR901465. I. Taxonomy, fermentation, isolation, physico-chemical properties, and biological activities J. Antibiot. 49, 1196-1203
    • (1996) J. Antibiot. , vol.49 , pp. 1196-1203
    • Nakajima, H.1    Sato, B.2    Fujita, T.3    Takase, S.4    Terano, H.5    Okuhara, M.6
  • 17
    • 84876916289 scopus 로고    scopus 로고
    • Genomics-guided discovery of thailanstatins A, B, and C as pre-mRNA splicing inhibitors and antiproliferative agents from Burkholderia thailandensis MSMB43
    • Liu, X., Biswas, S., Berg, M. G., Antapli, C. M., Xie, F., Wang, Q., Tang, M.-C., Tang, G.-L., Zhang, L., and Dreyfuss, G. (2013) Genomics-guided discovery of thailanstatins A, B, and C as pre-mRNA splicing inhibitors and antiproliferative agents from Burkholderia thailandensis MSMB43 J. Nat. Prod. 76, 685-693
    • (2013) J. Nat. Prod. , vol.76 , pp. 685-693
    • Liu, X.1    Biswas, S.2    Berg, M.G.3    Antapli, C.M.4    Xie, F.5    Wang, Q.6    Tang, M.-C.7    Tang, G.-L.8    Zhang, L.9    Dreyfuss, G.10
  • 18
    • 0036808433 scopus 로고    scopus 로고
    • GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. II. The effects on cell cycle progression and gene expression
    • Sakai, Y., Tsujita, T., Akiyama, T., Yoshida, T., Mizukami, T., Akinaga, S., Horinouchi, S., Yoshida, M., and Yoshida, T. (2002) GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. II. The effects on cell cycle progression and gene expression J. Antibiot. 55, 863-872
    • (2002) J. Antibiot. , vol.55 , pp. 863-872
    • Sakai, Y.1    Tsujita, T.2    Akiyama, T.3    Yoshida, T.4    Mizukami, T.5    Akinaga, S.6    Horinouchi, S.7    Yoshida, M.8    Yoshida, T.9
  • 19
    • 1842419704 scopus 로고    scopus 로고
    • TAN-1609 (herboxidiene): A microbial polyketide which blocks the cell-cycle at G-2 phase in human and murine tumor cells
    • Horiguchi, T., Shirasaki, M., and Tanida, S. (1996) TAN-1609 (herboxidiene): A microbial polyketide which blocks the cell-cycle at G-2 phase in human and murine tumor cells J. Takeda Res. Lab. 55, 149-159
    • (1996) J. Takeda Res. Lab. , vol.55 , pp. 149-159
    • Horiguchi, T.1    Shirasaki, M.2    Tanida, S.3
  • 20
    • 0035904404 scopus 로고    scopus 로고
    • FR901464: Total synthesis, proof of structure, and evaluation of synthetic analogues
    • Thompson, C. F., Jamison, T. F., and Jacobsen, E. N. (2001) FR901464: Total synthesis, proof of structure, and evaluation of synthetic analogues J. Am. Chem. Soc. 123, 9974-9983
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 9974-9983
    • Thompson, C.F.1    Jamison, T.F.2    Jacobsen, E.N.3
  • 21
    • 9244219683 scopus 로고    scopus 로고
    • Structure-activity relationship for FR901464: A versatile method tor the conversion and preparation of biologically active biotinylated probes
    • Motoyoshi, H., Horigome, M., Ishigami, K., Yoshida, T., Horinouchi, S., Yoshida, M., Watanabe, H., and Kitahara, T. (2004) Structure-activity relationship for FR901464: A versatile method tor the conversion and preparation of biologically active biotinylated probes Biosci. Biotechnol. Biochem. 68, 2178-2182
    • (2004) Biosci. Biotechnol. Biochem. , vol.68 , pp. 2178-2182
    • Motoyoshi, H.1    Horigome, M.2    Ishigami, K.3    Yoshida, T.4    Horinouchi, S.5    Yoshida, M.6    Watanabe, H.7    Kitahara, T.8
  • 22
    • 33847668813 scopus 로고    scopus 로고
    • Total syntheses, fragmentation studies, and antitumor/antiproliferative activities of FR901464 and its low picomolar analogue
    • Albert, B. J., Sivaramakrishnan, A., Naka, T., Czaicki, N. L., and Koide, K. (2007) Total syntheses, fragmentation studies, and antitumor/ antiproliferative activities of FR901464 and its low picomolar analogue J. Am. Chem. Soc. 129, 2648-2659
    • (2007) J. Am. Chem. Soc. , vol.129 , pp. 2648-2659
    • Albert, B.J.1    Sivaramakrishnan, A.2    Naka, T.3    Czaicki, N.L.4    Koide, K.5
  • 23
    • 78651417715 scopus 로고    scopus 로고
    • Structural requirements for the antiproliferative activity of pre-mRNA splicing inhibitor FR901464
    • Osman, S., Albert, B. J., Wang, Y. P., Li, M. S., Czaicki, N. L., and Koide, K. (2011) Structural requirements for the antiproliferative activity of pre-mRNA splicing inhibitor FR901464 Chemistry 17, 895-904
    • (2011) Chemistry , vol.17 , pp. 895-904
    • Osman, S.1    Albert, B.J.2    Wang, Y.P.3    Li, M.S.4    Czaicki, N.L.5    Koide, K.6
  • 25
    • 84868222063 scopus 로고    scopus 로고
    • Enantioselective total synthesis of pladienolide B: A potent spliceosome inhibitor
    • Ghosh, A. K. and Anderson, D. D. (2012) Enantioselective total synthesis of pladienolide B: A potent spliceosome inhibitor Org. Lett. 14, 4730-4733
    • (2012) Org. Lett. , vol.14 , pp. 4730-4733
    • Ghosh, A.K.1    Anderson, D.D.2
  • 27
    • 84885146374 scopus 로고    scopus 로고
    • Enantioselective syntheses of FR901464 and spliceostatin A: Potent inhibitors of spliceosome
    • Ghosh, A. K. and Chen, Z.-H. (2013) Enantioselective syntheses of FR901464 and spliceostatin A: Potent inhibitors of spliceosome Org. Lett. 15, 5088-5091
    • (2013) Org. Lett. , vol.15 , pp. 5088-5091
    • Ghosh, A.K.1    Chen, Z.-H.2
  • 28
    • 84868355027 scopus 로고    scopus 로고
    • The spliceosome as a target of novel antitumour drugs
    • Bonnal, S., Vigevani, L., and Valcarcel, J. (2012) The spliceosome as a target of novel antitumour drugs Nat. Rev. Drug Discovery 11, 847-859
    • (2012) Nat. Rev. Drug Discovery , vol.11 , pp. 847-859
    • Bonnal, S.1    Vigevani, L.2    Valcarcel, J.3
  • 31
    • 80052376000 scopus 로고    scopus 로고
    • Design, synthesis, and initial biological evaluation of a novel pladienolide analog scaffold
    • Gundluru, M. K., Pourpak, A., Cui, X., Morris, S. W., and Webb, T. R. (2011) Design, synthesis, and initial biological evaluation of a novel pladienolide analog scaffold MedChemComm 2, 904-908
    • (2011) MedChemComm , vol.2 , pp. 904-908
    • Gundluru, M.K.1    Pourpak, A.2    Cui, X.3    Morris, S.W.4    Webb, T.R.5
  • 33
    • 0036808675 scopus 로고    scopus 로고
    • GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities
    • Sakai, Y., Yoshida, T., Ochiai, K., Uosaki, Y., Saitoh, Y., Tanaka, F., Akiyama, T., Akinaga, S., and Mizukami, T. (2002) GEX1 compounds, novel antitumor antibiotics related to herboxidiene, produced by Streptomyces sp. I. Taxonomy, production, isolation, physicochemical properties and biological activities J. Antibiot. 55, 855-862
    • (2002) J. Antibiot. , vol.55 , pp. 855-862
    • Sakai, Y.1    Yoshida, T.2    Ochiai, K.3    Uosaki, Y.4    Saitoh, Y.5    Tanaka, F.6    Akiyama, T.7    Akinaga, S.8    Mizukami, T.9
  • 35
    • 80054757903 scopus 로고    scopus 로고
    • Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones
    • Pellicena, M., Kraemer, K., Romea, P., and Urpi, F. (2011) Total synthesis of (+)-herboxidiene from two chiral lactate-derived ketones Org. Lett. 13, 5350-5353
    • (2011) Org. Lett. , vol.13 , pp. 5350-5353
    • Pellicena, M.1    Kraemer, K.2    Romea, P.3    Urpi, F.4
  • 36
    • 78650955188 scopus 로고    scopus 로고
    • A stereoselective synthesis of (+)-herboxidiene/GEX1A
    • Ghosh, A. K. and Li, J. (2011) A stereoselective synthesis of (+)-herboxidiene/GEX1A Org. Lett. 13, 66-69
    • (2011) Org. Lett. , vol.13 , pp. 66-69
    • Ghosh, A.K.1    Li, J.2
  • 37
    • 54049149056 scopus 로고    scopus 로고
    • Total synthesis of GEX1A
    • Murray, T. J. and Forsyth, C. J. (2008) Total synthesis of GEX1A Org. Lett. 10, 3429-3431
    • (2008) Org. Lett. , vol.10 , pp. 3429-3431
    • Murray, T.J.1    Forsyth, C.J.2
  • 38
    • 34547952285 scopus 로고    scopus 로고
    • Total synthesis of herboxidiene/GEX 1A
    • Zhang, Y. and Panek, J. S. (2007) Total synthesis of herboxidiene/GEX 1A Org. Lett. 9, 3141-3143
    • (2007) Org. Lett. , vol.9 , pp. 3141-3143
    • Zhang, Y.1    Panek, J.S.2
  • 39
    • 0034583411 scopus 로고    scopus 로고
    • Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847
    • Banwell, M., McLeod, M., Premraj, R., and Simpson, G. (2000) Total synthesis of herboxidiene, a complex polyketide from Streptomyces species A7847 Pure Appl. Chem. 72, 1631-1634
    • (2000) Pure Appl. Chem. , vol.72 , pp. 1631-1634
    • Banwell, M.1    McLeod, M.2    Premraj, R.3    Simpson, G.4
  • 41
    • 84871492604 scopus 로고    scopus 로고
    • Comparison of splicing factor 3b inhibitors in human cells
    • Gao, Y., Vogt, A., Forsyth, C. J., and Koide, K. (2013) Comparison of splicing factor 3b inhibitors in human cells Chem. Bio. Chem. 14, 49-52
    • (2013) Chem. Bio. Chem. , vol.14 , pp. 49-52
    • Gao, Y.1    Vogt, A.2    Forsyth, C.J.3    Koide, K.4
  • 42
    • 0037118340 scopus 로고    scopus 로고
    • Stereospecific synthesis of cryptophycin 1
    • Li, L. H. and Tius, M. A. (2002) Stereospecific synthesis of cryptophycin 1 Org. Lett. 4, 1637-1640
    • (2002) Org. Lett. , vol.4 , pp. 1637-1640
    • Li, L.H.1    Tius, M.A.2
  • 43
    • 0021986893 scopus 로고
    • Chelation-controlled facially selective cyclocondenssation reactions of chiral alkoxy aldehydes-syntheses of a mouse androgen and of a carbon-linked disaccharide
    • Danishefsky, S. J., Pearson, W. H., Harvey, D. F., Maring, C. J., and Springer, J. P. (1985) Chelation-controlled facially selective cyclocondenssation reactions of chiral alkoxy aldehydes-syntheses of a mouse androgen and of a carbon-linked disaccharide J. Am. Chem. Soc. 107, 1256-1268
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1256-1268
    • Danishefsky, S.J.1    Pearson, W.H.2    Harvey, D.F.3    Maring, C.J.4    Springer, J.P.5
  • 44
    • 77949277387 scopus 로고    scopus 로고
    • Enantioselective construction of cis -2,6-disubstituted dihydropyrans: Total synthesis of (-)-centrolobine
    • Chaladaj, W., Kowalczyk, R., and Jurczak, J. (2010) Enantioselective construction of cis -2,6-disubstituted dihydropyrans: Total synthesis of (-)-centrolobine J. Org. Chem. 75, 1740-1743
    • (2010) J. Org. Chem. , vol.75 , pp. 1740-1743
    • Chaladaj, W.1    Kowalczyk, R.2    Jurczak, J.3
  • 45
    • 48249132008 scopus 로고    scopus 로고
    • Electrophile-induced ether transfer: Stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans
    • Kartika, R., Frein, J. D., and Taylor, R. E. (2008) Electrophile-induced ether transfer: Stereoselective synthesis of 2,6-disubstituted-3,4-dihydropyrans J. Org. Chem. 73, 5592-5594
    • (2008) J. Org. Chem. , vol.73 , pp. 5592-5594
    • Kartika, R.1    Frein, J.D.2    Taylor, R.E.3
  • 46
    • 0029129180 scopus 로고
    • The total synthesis of swinholide A. Part 2: A stereocontrolled synthesis of a c1-c15 segment
    • Paterson, I., Smith, J. D., and Ward, R. A. (1995) The total synthesis of swinholide A. Part 2: A stereocontrolled synthesis of a c1-c15 segment Tetrahedron 51, 9413-9436
    • (1995) Tetrahedron , vol.51 , pp. 9413-9436
    • Paterson, I.1    Smith, J.D.2    Ward, R.A.3
  • 47
    • 79953872085 scopus 로고    scopus 로고
    • Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold
    • Gerard, B., Marié, J.-C., Pandya, B. A., Lee, M. D., IV, Liu, H., and Marcaurelle, L. A. (2011) Large-scale synthesis of all stereoisomers of a 2,3-unsaturated C-glycoside scaffold J. Org. Chem. 76, 1898-1901
    • (2011) J. Org. Chem. , vol.76 , pp. 1898-1901
    • Gerard, B.1    Marié, J.-C.2    Pandya, B.A.3    Lee, M.D.I.V.4    Liu, H.5    Marcaurelle, L.A.6
  • 48
    • 0031562038 scopus 로고    scopus 로고
    • A simple asymmetric synthesis of cis -2,6-disubstituted tetrahydropyran acetic acid derivatives
    • Edmunds, A. J. F. and Trueb, W. (1997) A simple asymmetric synthesis of cis -2,6-disubstituted tetrahydropyran acetic acid derivatives Tetrahedron Lett. 38, 1009-1012
    • (1997) Tetrahedron Lett. , vol.38 , pp. 1009-1012
    • Edmunds, A.J.F.1    Trueb, W.2
  • 49
    • 79961049732 scopus 로고    scopus 로고
    • Sudemycins, novel small molecule analogues of FR901464, induce alternative gene splicing
    • Fan, L. Y., Lagisetti, C., Edwards, C. C., Webb, T. R., and Potter, P. M. (2011) Sudemycins, novel small molecule analogues of FR901464, induce alternative gene splicing ACS Chem. Biol. 6, 582-589
    • (2011) ACS Chem. Biol. , vol.6 , pp. 582-589
    • Fan, L.Y.1    Lagisetti, C.2    Edwards, C.C.3    Webb, T.R.4    Potter, P.M.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.